3-(4-tert-butylcyclohexyl)-4-hydroxynaphthalene-1,2-dione | 94015-46-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3-(4-tert-butylcyclohexyl)-4-hydroxynaphthalene-1,2-dione
• 英文别名: [14C]-58C80；2-hydroxy-3-(4-t-butylcyclohexyl)-1,4-naphthoquinone；2-(4-t-butylcyclohexyl)-3-hydroxy-1,4-naphthoquinone
• CAS: 94015-46-0
• 化学式: C₂₀H₂₄O₃
• 分子量: 312.409
• InChiKey: NWCVRXADYNRXCT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.73
• 重原子数：
  23.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  54.37
• 氢给体数：
  1.0
• 氢受体数：
  3.0

安全信息

• 海关编码：
  2914690090

反应信息

• 作为反应物：
  描述：

  3-(4-tert-butylcyclohexyl)-4-hydroxynaphthalene-1,2-dione 、 硫酸 以2%的产率得到
  参考文献：
  名称：

  HUDSON A. T.; PETHER M. J.; RANDALL A. W.; FRY M.; LATTER V. S.; MCHARDY +, EUR. J. MED. CHEM., 21,(1986) N 4, 271-275

  摘要：

  DOI：
• 作为产物：
  描述：

  2-(4-tert-Butylcyclohexyl)-3-chloronaphthalene-1,4-dione 生成 3-(4-tert-butylcyclohexyl)-4-hydroxynaphthalene-1,2-dione
  参考文献：
  名称：

  HUDSON, A. T.;RANDALL, A. W.

  摘要：

  DOI：

文献信息

• Medicaments for the treatment of toxoplasmosis
  申请人：THE WELLCOME FOUNDATION LIMITED

  公开号：EP0567162A1

  公开（公告）日：1993-10-27

  The present invention relates to the use of 2-[4-(4-chlorophenyl) cyclohexyl]-3-hydroxy-1,4-naphthoquinone or a physiologically acceptable salt or other physiologically funtional derivative thereof for the manufacture of a medicament for the treatment and/or prophylaxis of toxoplasmosis in animals, to pharmaceutical compositions for the treatment and/or prophylaxis of toxoplasmosis, comprising said compound as active ingredient and to a method of treating or preventing toxoplasmosis in an animal which comprises administering to said animal an effective amount of said compound.

  本发明涉及2-[4-(4-氯苯基)环己基]-3-羟基-1,4-萘醌或其生理可接受的盐或其他生理功能衍生物用于制造治疗和/或预防动物弓形虫病的药物，涉及包含该化合物作为活性成分的治疗和/或预防弓形虫病的药物组合物，以及涉及治疗或预防动物弓形虫病的方法，该方法包括向所述动物施用有效量的该化合物。
• [EN] NOVEL METHOD FOR PREPARATION OF ATOVAQUONE<br/>[FR] NOUVEAU PROCÉDÉ DE PRÉPARATION D'ATOVAQUONE
  申请人：LUPIN LTD

  公开号：WO2012153162A1

  公开（公告）日：2012-11-15

  Provided is a process of preparation of 2-[trans,-4-(4'-chlorophenyl)cyclohexyl]-3-hydroxy- 1,4-naphthoquinone, i.e. Atovaquone [I] which is cost effective, green, and eco-friendly process, without separation of any diastereomers or geometric isomers of intermediates obtained during the reactions. Also provided is separation of 'cis' and 'trans ' isomer of intermediates VI, VII and VIII through selective crystallization in an appropriate solvent. A method for converting 2-[cis,-4-(4'-chlorophenyl)cyclohexyl]-3-hydroxy-1,4-naphthoquinone to 2-[trans-4-(4'-chlorophenyl)cyclohexyl]-3-hydroxy-l,4-naphthoquinone in presence of Lewis/ Bronsted acid is also provided. A process for preparation of compound 2-(4-(4- chlorophenyl)- 1 -hydroxy cyclohexyl)-3,4-dihydronaphthalen- 1 (2H)-one [IV] comprising condensation of (1,2-dihydronaphthalen-4-yloxy)trimethylsilane [II] with 4-(4- chlorophenyl)cyclohexanone [III] in presence of Lewis acid in organic solvent. The invention also encompasses a highly efficient and atomeconomic process for synthesis of compound [III] i.e. 4-(4-chlorophenyl)cyclohexanone as well as a process for synthesis of 2-[cis-4-(4'- chlorophenyl)cyclohexyl]-3-hydroxy-l,4-naphthoquinone. Further provided is a process for isomerization of cis- Atovaquone i.e. 2-[cis-4-(4'-chlorophenyl)cyclohexyl]-3-hydroxy-l,4- naphthoquinone to tnms-Atovaquone i.e. 2-[trans-4-(4'-chlorophenyl)cyclohexyl]-3- hydroxy- 1,4-naphthoquinone in presence of Lewis acid.

  提供了一种制备2-[反式,-4-(4'-氯苯基)环己基]-3-羟基-1,4-萘醌，即阿托喹酮[I]的过程，这是一种具有成本效益、绿色、环保的过程，无需分离在反应过程中获得的中间体的对映异构体或几何异构体。还提供了通过在适当溶剂中选择性结晶来分离中间体VI、VII和VIII的'顺式'和'反式'异构体的方法。还提供了一种在路易斯/布朗斯特酸的存在的条件下将2-[顺式,-4-(4'-氯苯基)环己基]-3-羟基-1,4-萘醌转化为2-[反式-4-(4'-氯苯基)环己基]-3-羟基-1,4-萘醌的方法。还提供了一种制备化合物2-(4-(4-氯苯基)-1-羟基环己基)-3,4-二氢萘-1(2H)-酮[IV]的过程，包括(1,2-二氢萘-4-氧基)三甲基硅烷[II]与4-(4-氯苯基)环己酮[III]在有机溶剂中在路易斯酸的存在的条件下进行缩合。本发明还涵盖了高效且原子经济的合成化合物[III]即4-(4-氯苯基)环己酮的过程以及合成2-[顺式-4-(4'-氯苯基)环己基]-3-羟基-1,4-萘醌的过程。还提供了一种在路易斯酸的存在的条件下将顺式-阿托喹酮即2-[顺式-4-(4'-氯苯基)环己基]-3-羟基-1,4-萘醌异构化为反式-阿托喹酮即2-[反式-4-(4'-氯苯基)环己基]-3-羟基-1,4-萘醌的过程。
• Antiprotozoal compounds
  申请人：——

  公开号：US04485117A1

  公开（公告）日：1984-11-27

  1,4-Naphthoquinones of formula (I), methods for their preparation, pharmaceutical and veterinary formulations thereof and the use thereof in human and animal therapy are disclosed. ##STR1## Particularly preferred compounds of formula (I) are 2-(4'-t-butylcyclohexyl)-3-hydroxy-1,4-naphthoquinone and 2-hydroxy-3-(4'-t-pentylcyclohexyl)-1,4-naphthoquinone. The compounds are of value as antiprotozoal agents, in particular antimalarial and anticoccidial agents.

  本发明揭示了式（I）的1,4-萘醌，其制备方法，以及其在人类和动物治疗中的制药和兽药制剂。 ##STR1## 特别优选的式（I）化合物是2-(4'-叔丁基环己基)-3-羟基-1,4-萘醌和2-羟基-3-(4'-叔戊基环己基)-1,4-萘醌。这些化合物在抗原虫剂中具有价值，特别是在抗疟疾和抗球虫病剂方面。
• Naphthoquinones for the treatment and prophylaxis of pneumocystis carinii infections
  申请人：THE WELLCOME FOUNDATION LIMITED

  公开号：EP0362996A2

  公开（公告）日：1990-04-11

  The present invention relates to the use of known and novel naphthoquinones in the treatment and prophylaxis of Pneumocystis carinii infections, and for the manufacture of medicaments for the treatment and prophylaxis of P.carinii infections, novel formulations containing said compounds, and novel naphthoquinones of formula (VI): wherein R¹¹ and R¹² each represent =O and the dotted line represents a double bond between the 2 and 3 positions of the quinone ring, in which case R¹³ represents a group -OCOR⁵; a group OR⁶ or SR⁶; or a group NR⁷R⁸; or the dotted line represents double bonds at the 1,2 and 3,4 positions of the quinol ring and R¹¹, R¹² and R¹³ each represents a group -OCOR¹⁴, wherein R¹⁴ represents an optionally substituted C₁₋₁₀alkyl group.

  本发明涉及已知和新型萘醌在治疗和预防卡氏肺孢子虫感染中的用途，以及用于制造治疗和预防卡氏肺孢子虫感染的药物、含有上述化合物的新型制剂和式（VI）的新型萘醌： 其中 R¹¹ 和 R¹² 各自代表 =O，虚线代表醌环 2 和 3 位之间的双键，在这种情况下，R¹³ 代表基团 -OCOR⁵；基团 OR⁶ 或 SR⁶；或基团 NR⁷R⁸；或虚线代表喹啉环 1、2 和 3、4 位上的双键，且 R¹¹、R¹² 和 R¹³ 各代表一个基团 -OCOR¹⁴，其中 R¹⁴ 代表任选取代的 C₁₋₁₀烷基。
• Verwendung von Interferon und eines antimalarisch wirkenden Wirkstoffs zur Behandlung von Malaria Infektionen
  申请人：BOEHRINGER INGELHEIM INTERNATIONAL GmbH

  公开号：EP0490250A2

  公开（公告）日：1992-06-17

  Die vorliegende Erfindung betrifft die Verwendung von Arzneimitteln auf der Basis von mindestens einem antimalarisch wirkenden Mittel, welche zusätzlich ein Interferon, vorzugsweise Interferon-gamma (IFN-γ), enthalten. Das erfindungsgemäße Arzneimittel findet Verwendung bei der Behandlung der klinischen Malaria.

  本发明涉及以至少一种抗疟药物为基础的药剂的使用，这些药剂另外含有一种干扰素，最好是γ干扰素（IFN-γ）。根据本发明的药物可用于治疗临床疟疾。